Skip to main content

Advertisement

SpringerLink
Log in

Employing nano-SnFe2O4 in the synthesis of arylbenzimidazoles, the computational study of the reaction mechanism, and examining the products as putative human transmembrane protein activators

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

In this work, the efficient and green method has been presented to prepare arylbenzimidazoles via an aqueous, one-pot reaction. The products were obtained using the reaction between aldehydes, malononitrile, and 1,2-phenylenediamine in water as a solvent at room temperature. SnFe2O4 nanoparticles were used as the heterogeneous catalyst at room temperature under an inert atmosphere. The morphology and composition of the catalyst have been defined by SEM, XRD, UV–Vis, FTIR, and Raman spectroscopy. Ten different arylbenzimidazoles were prepared in 70–98% yield. The structural properties of the synthesized arylbenzimidazoles were investigated using FT-IR, NMR, and mass spectrometry. The plausible mechanism was studied using DFT calculations. Furthermore, molecular docking simulations identified the synthesized arylbenzimidazoles as an activator of transmembrane proteins of the human innate immune system. The usefulness of the product as a Human transmembrane Protein activator was proved using Docking studies.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Scheme 1
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

Availability of data and materials

All data all available and could be sent on request from the corresponding author. Characterization data associated with this article a solvent including the copies of 1H and 13CNMR, mass and FT-IR spectra of reported arylbenzimidazoles derivatives is available at a single file. Moreover, all extra data related to the computational parts of the manuscript are reported.

References

  1. E. Vitaku, D.T. Smith, J.T. Njardarson, J. Med. Chem. 57(24), 10257 (2014)

    Article  CAS  PubMed  Google Scholar 

  2. K.C.S. Achar, K.M. Hosamani, H.R. Seetharamareddy, Eur. J. Med. Chem. 45(5), 2048 (2010)

    Article  CAS  PubMed  Google Scholar 

  3. A.T. Mavrova, D. Yancheva, N. Anastassova, K. Anichina, J. Zvezdanovic, A. Djordjevic, D. Markovic, A. Smelcerovic, Bioorg. Med. Chem. 23(19), 6317 (2015)

    Article  CAS  PubMed  Google Scholar 

  4. Ş Demirayak, U.A. Mohsen, A.Ç. Karaburun, Eur. J. Med. Chem. 37(3), 255 (2002)

    Article  CAS  PubMed  Google Scholar 

  5. K. Paul, A. Sharma, V. Luxami, Bioorg. Med. Chem. Lett. 24(2), 624 (2014)

    Article  CAS  PubMed  Google Scholar 

  6. R.V. Shingalapur, K.M. Hosamani, R.S. Keri, M.H. Hugar, Eur. J. Med. Chem. 45(5), 1753 (2010)

    Article  CAS  PubMed  Google Scholar 

  7. Z.M. Nofal, A.M. Srour, W.I. El-Eraky, D.O. Saleh, A.S. Girgis, Eur. J. Med. Chem. 63, 14 (2013)

    Article  CAS  PubMed  Google Scholar 

  8. M. Tunçbilek, T. Kiper, N. Altanlar, Eur. J. Med. Chem. 44(3), 1024 (2009)

    Article  PubMed  Google Scholar 

  9. T. Hisano, M. Ichikawa, K. Tsumoto, M. Tasaki, Chem. Pharm. Bull. 30(8), 2996 (1982)

    Article  CAS  Google Scholar 

  10. M.T. Migawa, J.L. Girardet, J.A. Walker, G.W. Koszalka, S.D. Chamberlain, J.C. Drach, L.B. Townsend, J. Design, Med. Chem. 41(8), 1242 (1998)

    Article  CAS  Google Scholar 

  11. Y. Luo, J.P. Yao, L. Yang, C.L. Feng, W. Tang, G.F. Wang, J.P. Zuo, W. Lu, Bioorg. Med. Chem. 18(14), 5048 (2010)

    Article  CAS  PubMed  Google Scholar 

  12. J.A. Asensio, P. Gómez-Romero, Fuel Cells 5(3), 336 (2005)

    Article  CAS  Google Scholar 

  13. J. Jayabharathi, V. Thanikachalam, K. Jayamoorthy, Photochem. Photobiol. Sci. 12, 1761 (2013)

    Article  CAS  PubMed  Google Scholar 

  14. Y. Bai, J. Lu, Z. Shi, B. Yang, Synlett 2001(04), 544 (2001)

    Article  Google Scholar 

  15. H. Hikawa, R. Ichinose, S. Kikkawa, I. Azumaya, Asian. J. Org. Chem. 7(2), 416 (2018)

    CAS  Google Scholar 

  16. K. Bahrami, M. Khodaei, I. Kavianinia, Synthesis 2007(04), 547 (2007)

    Article  Google Scholar 

  17. S.M. Arde, A.D. Patil, A.H. Mane, P.R. Salokhe, R.S. Salunkhe, Res. Chem. Intermed. 46, 5069 (2020)

    Article  CAS  Google Scholar 

  18. H.D. Hanoon, E. Kowsari, M. Abdouss, H. Zandi, M.H. Ghasemi, Res. Chem. Intermed. 43, 1751 (2017)

    Article  CAS  Google Scholar 

  19. R. Sharma, M. Abdullaha, S.B. Bharate, Asian. J. Org. Chem. 6(10), 1370 (2017)

    CAS  Google Scholar 

  20. T.A. To, Y.H. Vo, H.T.T. Nguyen, P.T.M. Ha, S.H. Doan, T.L.H. Doan, S. Li, H.V. Le, T.N.N. Tu, T.S. Phan, J. Catal. 370, 11 (2019)

    Article  CAS  Google Scholar 

  21. R. Chopra, M. Kumar, V. Neelam Bhalla, Green Chem. 21, 3666 (2019)

    Article  CAS  Google Scholar 

  22. V. Sriramoju, S. Kurva, S. Madabhushi, New J. Chem. 42(5), 3188 (2018)

    Article  CAS  Google Scholar 

  23. I. Bhatnagar, M.V. George, Tetrahedron 24(3), 1293 (1968)

    Article  CAS  Google Scholar 

  24. P. Gogoi, D. Konwar, Tetrahedron Lett. 47(1), 79 (2006)

    Article  CAS  Google Scholar 

  25. M.T. Maghsoodlou, N. Hazeri, M. Lashkari, F.N. Shahrokhabadi, B. Naghshbandi, S. Kazemi-doost Salahi, Res. Chem. Intermed. 41, 6985 (2015)

    Article  CAS  Google Scholar 

  26. S. Karhale, K. Patil, C. Bhenki, G. Rashinkar, V. Helavi, Res. Chem. Intermed. 42, 7257 (2016)

    Article  CAS  Google Scholar 

  27. M.T. Jafari-Chermahini, H. Tavakol, W. Salvenmoser, ChemistrySelect 5(3), 968 (2020)

    Article  CAS  Google Scholar 

  28. M.T. Jafari-Chermahini, H. Tavakol, ChemistrySelect 4(6), 1895 (2019)

    Article  CAS  Google Scholar 

  29. M.T. Jafari-Chermahini, H. Tavakol, ChemistrySelect 6(9), 2360 (2021)

    Article  CAS  Google Scholar 

  30. F.C. Zhou, Y.H. Sun, S. Liu, J.M. Nan, Solid State Ion. 296, 163 (2016)

    Article  CAS  Google Scholar 

  31. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Revision D.01.

  32. A.D. McLean, G.S. Chandler, J. Chem. Phys. 72(10), 5639 (1980)

    Article  CAS  Google Scholar 

  33. C. Peng, P.Y. Ayala, H.B. Schlegel, M.J. Frisch, J. Comput. Chem. 17(1), 49 (1996)

    Article  CAS  Google Scholar 

  34. C. Gonzalez, H.B. Schlegel, J. Phys. Chem. 94(14), 5523 (1990)

    Article  CAS  Google Scholar 

  35. B. Mennucci, E. Cancès, J. Tomasi, J. Phys. Chem. B 101(49), 10506 (1997)

    Article  CAS  Google Scholar 

  36. SwissDock. http://www.swissdock.ch.

  37. A. Grosdidier, V. Zoete, O. Michielin, Nucl. Acids Res. 39(2), W270 (2011)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  38. R.H. Stote, D.J. States, M. Karplus, J. Chim. Phys. 88, 2419 (1991)

    Article  CAS  Google Scholar 

  39. X. Cong, Z. Yuan, Y. Du, B. Wu, D. Lu, X. Wu, L. Gu, J. Biol. Chem. 294(30), 11420 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. P. Gao, D.J. Patel, https://doi.org/10.2210/pdb4loh/pdb.

  41. S.K. Burley, H.M. Berman, C. Bhikadiya, C. Bi, L. Chen, L.D. Costanzo, C. Christie, J.M. Duarte, S. Dutta, Z. Feng, S. Ghosh, D.S. Goodsell, R.K. Green, V. Guranovic, D. Guzenko, B.P. Hudson, Y. Liang, R. Lowe, E. Peisach, I. Periskova, C. Randle, A. Rose, M. Sekharan, C. Shao, Y.P. Tao, Y. Valasatava, M. Voigt, J. Westbrook, J. Young, C. Zardecki, M. Zhuravleva, G. Kurisu, H. Nakamura, Y. Kengaku, H. Cho, J. Sato, J.Y. Kim, Y. Ikegawa, A. Nakagawa, R. Yamashita, T. Kudou, G.J. Bekker, H. Suzuki, T. Iwata, M. Yokochi, N. Kobayashi, T. Fujiwara, S. Velankar, G.J. Kleywegt, S. Anyango, D.R. Armstrong, J.M. Berrisford, M.J. Conroy, J.M. Dana, M. Deshpande, P. Gane, R. Gáborová, D. Gupta, A. Gutmanas, A. Koča, L. Jaroslav, S. Mir, A. Mukhopadhyay, N. Nadzirin, S. Nair, A. Patwardhan, T. Paysan-Lafosse, L. Pravda, O. Salih, D. Sehnal, M. Varadi, R. Vařeková, J.L. Markley, J.C. Hoch, P.R. Romero, K. Baskaran, D. Maziuk, E.L. Ulrich, J.R. Wedell, H. Yao, M. Livny, Y.E. Ioannidis, Nucleic Acids Res. 47(D1), D520 (2018)

    Google Scholar 

  42. P. Schmidtke, V. LeGuilloux, J. Maupetit, P. Tuffïry, Nucleic Acids Res. 38, W582 (2010)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  43. V.L. Guilloux, P. Schmidtke, P. Tuffery, BMC Bioinf. 10(1), 168 (2009)

    Article  Google Scholar 

  44. Fpocket webserver. http://bioserv.rpbs.univ-paris-diderot.fr/fpocket/.

  45. Ressource Parisienne en Bioinformatique Structurale. http://bioserv.rpbs.univ-paris-diderot.fr/index.html.

  46. The PyMOL Molecular Graphics System, Version 1.8, 2015.

  47. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, T.E. Ferrin, J. Comput. Chem. 25(13), 1605 (2004)

    Article  CAS  PubMed  Google Scholar 

  48. F.J. Berry, C. Greaves, J.G. McManus, M. Mortimer, G. Oates, J. Solid State Chem. 130(2), 272 (1997)

    Article  CAS  Google Scholar 

  49. D.M. Smilgies, J. Appl. Crystallogr. 42(6), 1030 (2009)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  50. F. Jahan, M.H. Islam, B.E. Smith, Sol. Energy Mater Sol. Cells 37(3), 283 (1995)

    Article  CAS  Google Scholar 

  51. Y. Jia, D.H. Kim, T. Lee, S. Kang, B.W. Lee, S.J. Rhee, C. Liu, RSC Adv. 6, 76542 (2016)

    Article  CAS  Google Scholar 

  52. D.L.A. deFaria, S. VenâncioSilva, M.T. deOliveira, Mater. Charact 28(11), 873 (1997)

    CAS  Google Scholar 

  53. D.B. Ramachary, G.B. Reddy, Org. Biomol. Chem. 4, 4463 (2006)

    Article  CAS  PubMed  Google Scholar 

  54. K. Kapoor, S. Kumar, Synlett 2007(18), 2809 (2007)

    Article  Google Scholar 

  55. M.F. Kamte, C. Wagner, W. Schaefer, J. Coord. Chem. 57(1), 55 (2004)

    Article  CAS  Google Scholar 

  56. C. Yu, P. Guo, C. Jin, W. Su, J. Chem. Res. 2009(5), 333 (2009)

    Article  Google Scholar 

  57. K. Itoh, H. Ishida, H. Chikashita, Chem. Lett. 11(7), 1117 (1982)

    Article  Google Scholar 

  58. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.M. Basset, Chem. Rev. 111(5), 3036 (2011)

    Article  CAS  PubMed  Google Scholar 

  59. J. Li, S. Bénard, L. Neuville, J. Zhu, Org. Lett. 14(23), 5980 (2012)

    Article  CAS  PubMed  Google Scholar 

  60. M.A. Chari, D. Shobha, E.R. Kenawy, S.S. Al-Deyab, B.V.S. Reddy, A. Vinu, Tetrahedron Lett. 51(39), 5195 (2010)

    Article  CAS  Google Scholar 

  61. X. He, Y. Wu, W. Jin, X. Wang, C. Wu, Y. Shang, Appl. Organomet. Chem. 32(4), 4284 (2018)

    Article  Google Scholar 

  62. M. Largeron, K. Nguyen, Synthesis 50(2), 241 (2017)

    Article  Google Scholar 

  63. J. Yu, Y. Xia, M. Lu, Appl. Organomet. Chem. 28(10), 764 (2014)

    Article  CAS  Google Scholar 

  64. S. Park, J. Jung, E.J. Cho, Eur. J. Org. Chem. 2014(19), 4148 (2014)

    Article  CAS  Google Scholar 

  65. H. Sharghi, M. Aberi, M.M. Doroodmand, Adv. Synth. Catal. 350(14), 2380 (2008)

    Article  CAS  Google Scholar 

  66. Z. Chen, C.S. Wannere, C. Corminboeuf, R. Puchta, P.V.R. Schleyer, Chem. Rev. 105(10), 3842 (2005)

    Article  CAS  PubMed  Google Scholar 

  67. P.E. Blöchl, Phys. Rev. B 50(24), 17953 (1994)

    Article  Google Scholar 

  68. J.P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 77, 3865 (1996)

    Article  CAS  PubMed  Google Scholar 

  69. G. Kresse, J. Furthmüller, Phys. Rev. B 54, 11169 (1996)

    Article  CAS  Google Scholar 

  70. A.D. Becke, K.E. Edgecombe, J. Chem. Phys. 92(9), 5397 (1990)

    Article  CAS  Google Scholar 

  71. K. Momma, F. Izumi, J. Appl. Cryst. 44(6), 1272 (2011)

    Article  CAS  Google Scholar 

  72. J.M. Ramanjulu, G.S. Pesiridis, J. Yang, N. Concha, R. Singhaus, S.Y. Zhang, J.L. Tran, P. Moore, S. Lehmann, H.C. Eberl, M. Muelbaier, J.L. Schneck, J. Clemens, M. Adam, J. Mehlmann, J. Romano, A. Morales, J. Kang, L. Leister, T.L. Graybill, A.K. Charnley, G. Ye, N. Nevins, K. Behnia, A.I. Wolf, V. Kasparcova, K. Nurse, L. Wang, Y. Li, M. Klein, C.B. Hopson, J. Guss, M. Bantscheff, G. Bergamini, M.A. Reilly, Y. Lian, K.J. Duffy, J. Adams, K.P. Foley, P.J. Gough, R.W. Marquis, J. Smothers, A. Hoos, J. Bertin, Nature 564(7736), 439 (2018)

    Article  CAS  PubMed  Google Scholar 

  73. S.M. Haag, M.F. Gulen, L. Reymond, A. Gibelin, L. Abrami, A. Decout, M. Heymann, F.G. VanderGoot, G. Turcatti, R. Behrendt, A. Ablasser, Nature 559(7713), 269 (2018)

    Article  CAS  PubMed  Google Scholar 

  74. X. Cong, Z. Yuan, Y. Du, B. Wu, D. Lu, X. Wu, Y. Zhang, F. Li, B. Wei, J. Li, J. Wu, S. Xu, J. Wang, J. Qi, G. Shang, L. Gu, J. Biol. Chem. 294(30), 11420 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  75. X. Zhang, H. Shi, J. Wu, X. Zhang, L. Sun, C. Chen, Z.J. Chen, Mol. Cell 51(2), 226 (2013)

    Article  CAS  PubMed  Google Scholar 

  76. P. Gao, M. Ascano, T. Zillinger, W. Wang, P. Dai, A.A. Serganov, B.L. Gaffney, S. Shuman, R.A. Jones, L. Deng, G. Hartmann, W. Barchet, T. Tuschl, D.J. Patel, Cell 154(4), 748 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  77. Cloud 3D-QSAR. http://chemyang.ccnu.edu.cn/ccb/server/cloud3dQSAR/

  78. A. Rostami, O. Pourshiani, Y. Navasi, N. Darvishi, S. Saadati, New J. Chem. 41(4), 9033 (2017)

    Article  CAS  Google Scholar 

  79. M. Karthik, P. Suresh, New J. Chem. 42(22), 17931 (2018)

    Article  CAS  Google Scholar 

  80. V. Sankar, P. Karthik, B. Neppolian, B. Sivakumar, New J. Chem. 44(3), 1021 (2020)

    Article  CAS  Google Scholar 

  81. H. Mohammadi, C. Karami, M. Bahri, M. Mahmoudian, M.A. Taher, Inorg. Nanomet. Chem. 47(9), 1334 (2017)

    CAS  Google Scholar 

  82. K. Bahrami, M.M. Khodaei, F. Naali, Synlett 4, 569 (2009)

    Article  Google Scholar 

  83. P.K. Sahu, RSC Adv. 7, 42000 (2017)

    Article  CAS  Google Scholar 

  84. M.A. Chari, D. Shobha, E.R. Kenawy, S.S. Al-Deyab, B.V.S. Reddy, A. Vinu, Tetrahedron Lett. 51, 5195 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank the Isfahan University of Technology for financially support of this research and Rakhsh National High-Performance Computing Center for the computational facility.

Funding

No fund is received for this work.

Author information

Authors and Affiliations

  1. Department of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, Iran

    Mohammad Taqi Jafari-Chermahini & Hossein Tavakol

Authors
  1. Mohammad Taqi Jafari-Chermahini
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hossein Tavakol
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

M.T.J. designed the study, performed calculations and experiment, analysed data and wrote the draft. H.T. analysed data, prepared final format, and modified the manuscript.

Corresponding author

Correspondence to Hossein Tavakol.

Ethics declarations

Competing interests

The Authors declare that there is no financial or personal interest.

Ethical approval

This work does not include any human and/or animal studies.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 4970 kb)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jafari-Chermahini, M.T., Tavakol, H. Employing nano-SnFe2O4 in the synthesis of arylbenzimidazoles, the computational study of the reaction mechanism, and examining the products as putative human transmembrane protein activators. Res Chem Intermed 49, 4065–4086 (2023). https://doi.org/10.1007/s11164-023-05065-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-023-05065-9

Keywords

Search

Navigation